Insecure
by Trekkiehood
Summary: Jack Kelly, the confident cocky strike leader, is known for always being so sure of himself! Except he isn't. In fact, he's a very broken, insecure boy. Every insecurity and self-hatred has a beginning seed that causes him to look at himself in a different way. His is friends are only now starting notice. Each chapter is a separate story. WARNING: Mental/Physical abuse, self-hatred
1. Art

**A new story! Really it's more like stories. It's a group of short stories of Jack's friends finding out just how insecure he is, and you as a reader, finding out why.**

**With that being said, every chapter is going to deal heavily with verbal abuse. A few chapters have physical abuse, but all of it is very verbal. If you don't like that, you can skip the italics part of each chapter.**

**Italics is Jack's pov, the rest is the other characters.**

**This chapter is pre-strike.**

**Anyway, please enjoy!**

**WARNING: Verbal abuse, a child gets slapped (if this is a no for you, skip the italics).**

~TH~

Crutchie hummed quietly on the rooftop. It had been a good day of selling, now he had his back pressed against the wall, watching the sunset. Jack was on the other side of the roof, trying to finish a drawing while there was still light in the sky.

"Watcha workin' on?"

Jack's head shot up, startled.

_"What are you working on, boy?" The large man staggered over to the table where the six-year-old was sitting at the small table, pencil in hand._

_Young Jack Kelly looked up his father with wide, scared eyes. "I-I's just drawing."_

_"Ha!" The drunk man scoffed, snatching the paper out from under the boy's hands. "You call this drawin'?" He studies the paper, wadding it up and throwing it across the room. "This is nothing but scribbles!"_

_"I-it's the flowers. F-from, from Mamma's fun'ral."_

_He growled bringing a hand down on his son's face. Jack's head snapped to the side as the man grabbed the small pencil out of his hand, breaking it two._

_"You can't draw worth nothin' boy so go ahead and get that through your thick skull. You's mamma could draw, but she's dead and ain't no one gonna ever be as good as her. So stop wasting your time and go do something useful!"_

_Jack tried desperately to keep the tears out of his eyes. "Yes, P-papa," He managed from trembling lips, standing and rushing out of the room._

Jack hadn't moved, staring into the distance as his chest rose and fell a bit too fast. He was remembering something, though Crutchie couldn't be sure exactly what. He knew the best thing to do for the moment was to just leave him alone.

"Nothin'." the older boy finally spoke. "I ain't workin' on nothin'. Just messin' around."

Crutchie hobbled over to his friend. He didn't want to crowd Jack, but he didn't want to leave him alone either. "Can I see?"

Jack pressed the sheet of paper to his chest giving a slightly fearful look at his best friend.

"Please?"

His hands came down a little, revealing to Crutchie a beautiful drawing of a sunset. "Jackie, it's beautiful." He gasped. "I di'n know you could draw." He reached for the paper, only for the older boy to jerk it back to himself.

"I can't. It was just somethin' for my hand to do, ta keep it busy."

Crutchie pulled Jack's hand away, taking the paper in his own. "This is amazing Jack. It's the sunset in black and white!"

"It's nothin' Crutch." he reached for the drawing, but the younger boy kept studying it.

"No, it ain't. It's somethin' for sure. Can I keep it?"

He looked at his friend. Jack blinked at him.

"Why would you want it?" He said, sounding utterly bewildered.

The crippled boy laughed, "Because it's good Jack. It's pretty. Makes me smile. So can I keep it?"

"If you really want to." Jack shrugged, "Jus'," he paused a moment while Crutchie looked at him expectantly. "Jus' don't show it to no one."

Crutchie nodded, but he didn't understand. If he could make something so beautiful, he'd want everyone to see it.

"I, uh, I should probably go make sure the boys is gettin' to bed." The Newsies leader practically jumped to his feet before heading down the latter.

Crutchie watched him go, still confused by his normally confident friend's actions. He looked at the picture and smiled. It truly was breathtaking.

~TH~

**That is the first part!**

**Every chapter will deal with a different insecurity Jack has. If you have any ideas for chapters, let me know! I have four written at the moment and will be uploading them over the next couple days.**

**Thanks so much for reading! Please comment if you enjoyed it or have any critiques or suggestions!**

**Follow me on tumblr Trekkiehood.**

**Gosh bless,**  
**Jamie**


	2. Deserved

**Another story! In this one, Race finds out that Jack thinks he deserves all the bad things that happen to him.**

**Pre-strike**

**WARNING: Highly violent, description of child abuse, extremely abusive and toxic words (In italics) The rest has description of injury and incoherent screaming of self-blame. It's a really dark chapter.**

**~TH~**

Race growled, storming up the Lodging House steps. Only he would forget his pape money. He was way too stressed. He hated being in charge. Curse the Refuge and that stupid Spider. He couldn't do this. Not without-

"Jack?"

The Manhattan leader was laying on the bunk closest to the window. He was curled in on himself, facing the wall, his back to the rest of the room.

Racetrack carefully approached him. The older boy looked rough. "Jackie, can you hear me?" He reached out, lightly touching his friend.

Jack jerked back, gasping. He pushed out weakly hitting Race in the stomach. He sat up, blinking, looking at his concerned friend with only vague recognition.

"Jack, hey, hey, Jackie," Race lifted his hands in surrender, "It's just me, Race." In the brief moment of contact, he had felt the heat radiating off of his friend. He was clearly fevered, and from the looks of it, in pain.

"Race?" A croaky voice questioned.

"Yeah, yeah, it's me." He paused a moment while glassy eyes stared at him. "I think you've got a fever. Are you sick?"

Jack weakly shook his head, "Think, think it's infected." He mumbled.

"What is?" Race took a step forward, even more worry rising up.

"Muh back." The boy squeezed his eyes shut. "R maybe it's muh ribs. I o'n know." He was clearly delirious as he swayed back forth on the bed, seeming to will himself awake.

"Can I see?"

Jack shook his head adamantly.

"Come on Jackie, if you don't let me see it, it's just gonna get worse."

The boy in question groaned before going to undo the buttons with shaking fingers. Race began to help him unto the buttons and slip the shirt off. It was easy to see the dark bruises along the ribs. Some of them had to be broken. But Jack had said his back...

"D'ya think you could lie down for a minute? So's I can see your back?"

Jack didn't respond as he turned on his side.

It was bad. There were bruises, cuts and even several lashes. One of which was red and puffy. Infected.

Race went and got some water and a rag. This was going to hurt

"If I ever get my hands on that Spider I'll-"

"S'not his fault."

Race stopped, his hand just dipped into the water. "Then whose fault was it?" Who else would have done it?

"S'my fault."

_He was shoved down the remaining_ _stairs, barely able to stay on his feet._

_"You're going to get it now boy. You should learn to control your mouth. Shirt off."_

_Jack glared defiantly at his captor, "I ain't doin' nothin' for you Spider."_

_Snyder smiled, anger gleaming in his eyes. He shoved the boy against the wall, his hand wrapping around his throat._

_Jack gasped, clawing at the hands that kept him from breathing. Finally, he was released. He fell to the ground gasping for air._

_"Let's try this again." The older man stood over him. "Shirt off."_

_The boy reluctantly did as he was told, knowing what was coming, but not sure he could survive another attempt at strangulation. He had heard rumours of what was to come next. Spider liked to beat on him, but he'd never pushed him far enough to actually be brought to the basement._

_"Very good boy. Think of how much simpler your life would be if you just did as you were told."_

_Jack used the wall to help him stand to his feet. "Why do you like this so much? What kind of sick person likes to hurt other people?"_

_"You have it all wrong boy." Snyder clicked his tongue. "You think I like to hurt you? No, I'm just the only one brave enough to give you what you deserve."_

_"No one deserves this." Jack spat back._

_The older man shook his head, "That's where you're wrong. You deserve the pain. You killed your mother."_

_"What?" Jack shrieked angrily. He threw himself at Snyder and was answered by being thrown to the ground._

_"She was overworked, I can see why after dealing with you. I don't know how she did it so long! It's a miracle your father stuck around for a full seven. Especially since he clearly didn't have the courage to give you the beating you deserve."_

_Jack whimpered as the man's boot repeatedly came down on his ribs. He cried out when a particular harsh kick caused a loud crack in his chest. He curled in on himself, trying to get it to stop._

_He was pulled up by the hair until he was looking the Spider in the eyes. "You need to understand, boy, you are nothing. You deserve everything you get. You're here because no one cares about you. Everything that happens is your fault."_

_The boy couldn't keep from sobbing as he was dropped onto the floor. Footsteps walked away for a brief moment before coming back._

_"Remember, you deserve this boy."_

_There was a snap, then a pain like Jack had never felt before spread across his back._

_"Say it."_

_He couldn't. He couldn't do anything but force himself to breathe._

_Another strike."Say it boy, say you deserve this."_

_"I-I d-d'srve this."_

_"That's right." Another slash. "Now say you're worthless."_

_"'M worthless." He screamed as the whip came down again._

_"Now you're learning boy. Say it again, whose fault is this?"_

_"Mine!"_

_This went on until Jack mercifully passed out._

"What do you mean it's your fault?" Race asked, bewildered.

Jack curled in even more on himself. "'Smy fault."

"Jack! None of this is your fault!" The younger boy didn't know how to respond. How could his leader, his friend, even possibly believe that?

The older boy didn't answer and after a moment, Race began to clean the infected stripe.

Jack jerked violently, "I'm sorry, I'm sorry! It's my fault, it's mine!"

"Hey, hey, hey," Race tried to comfort him, "Jack, you're fine. It's just me. I's gotta clean it. You haven't done nothing wrong!" He felt nearly as frantic as his friend seemed to be.

"I deserve it! I'm sorry! It's my fault!"

No matter what Racetrack did, he wouldn't stop screaming, so he continued cleaning the wound with tears in his eyes.

~N~

A week later, Jack's fever broke. He was back to work in two. Race couldn't stop thinking about everything Jack had said.

When it was just him and Jack in the Lodging House, he approached him. "Hey, Jackie,"

"Hm?" The oldest Newsie turned to face him a slight and rare smile on his lips. Race almost lost his resolve.

"You know it's not your, fault, right? Everything he did to ya, it's not okay, no one deserves that."

Jack's smile faltered a moment before an extremely tight smile took his face. "'Course I know. Why ya askin'?"

"Jus'... makin' sure." He shrugged.

The older boy nodded, before turning and walking away.

Race had to say, that was quite possibly the least convincing lie Jack had ever told him.

**~TH~**

**There you go! Will probably post the next chapter tomorrow.**

**I beg you to leave comments. I don't want to be needy, but I desperately validation that my content isn't absolute trash...**

**Next chapter features Davey and Jack discussing Jack's importance to the Newsies.**

**Until then!**

**God bless,**  
**Jamie**


	3. Better

**In this one, Davey tries to convince Jack that the boys love him as much as he loves them.**

**WARNING: Verbal Abuse, Minor Physical Abuse, Mean Delancy's, Some Ableist Language (italics) and the whole thing deals with Self-doubt**

**Post-strike**

**~TH~**

David approached his friend with a concerned frown. Jack looked terrible. He had deep bags under his eyes, he looked weak and... hungry. He looked very hungry.

"Hey, Jack."

The boy in question looked up, seeming almost startled, before relaxing into a tired smile. "Hey, Davey."

David was mildly surprised that his friend was so far back in the paper line. He was normally one of the first people there. "Late start?"

Jack grunted, rubbing at his face. "Romeo's sick. Di'n want to take his medicine. Took a while to convince him."

Oh. Sick. Medicine. No wonder Jack looked half-dead. Davey shook his head, Jack did more for these boys than some parents did for their own children."You know," he said casually as they moved up in the line. "The boys are really lucky to have you."

The leader of the Newsies let out a breathy laugh, "No they ain't." He slammed his money down before grabbing his papers.

_"Well Jackie-boy, I've been waiting a long time for this." Oscar closed in on him, his brother shadowing behind him. "We was told to make sure you behave, but we all know that you ain't gonna. So let's just get right to it yeah?"_

_Jack began backing up until his back hit the wall. He ducked as Oscar aimed a punch at his face._

_"Careful Oscar, don't want it to look too obvious." Morris sneered. "He has an appointment later today." It was said with a gleam in his eyes, a smirk gracing his lips._

_Jack pushed Oscar away from him and jumped across the old printing press he had slept on the night before. The brothers began to corner him again. Jack hadn't felt this trapped since he was last at the Refuge. The Refuge. Where Crutchie was. Where they were going to take his boys if he didn't do what they told him to._

_"I find this whole predicament funny." The younger brother closed in on him, pounding his fist into his hand. "You act like you're such a great leader, but, you couldn't even keep that crippled friend of yours from the Spider."_

_Jack was about to say something, but he was caught off guard by Morris grabbing his arms from behind, pinning him against the older brother's chest._

_"And now you gotta choose." Oscar continued closing in on him. "Do you leave, do your own thing and get them all thrown in the Refuge, so they hate ya," He punches Jack in the stomach with his brass knuckles, causing the boy to gasp. "Or, do you do what Pulitzer says, call off the strike, so they all hate ya." He laughed throwing another fist._

_Jack sputtered to catch his breath, "The-they wouldn't. They'd understand." He didn't know if he was trying to convince the brothers or himself._

_"They'd turn on you, Jackie." The younger Delancy shook his head, "The second you tell 'em to quit, they're gonna turn against ya."_

_"They-they wouldn't. They'd let me explain-" He was cut off by another swift punch._

_"I'm tellin' ya. They've been waitin' for this. The second you turn, they've got someone else lined up to take the lead. They know they'd be better off without ya, just haven't had a reason to tell ya yet. They deserve better than you, Kelly, and they know it."_

_Morris dropped him to the ground, aiming a swift kick at Jack's sore stomach. The brother started to walk away._

_"You're wrong." Jack pushed himself up. "They'll understand. They'll let me explain."_

_Oscar shook his head, "Just wait Jackie-boy, they won't even let you finish what you want ta say before they turn against ya. But hey, it's better than the Refuge right?" The boys laughed as they left the room._

_He remembered those words when he was at the rally trying to explain. They didn't even let him finish talking before they turned on him._

"Come on, Jack," David grabbed his papers before following his friend. "The boys love you!"

"They deserve better than me." He said it with so little emotion that it actually scared the other newsie.

"You're the best thing to ever happen to these boys!"

Jack laughed, "You got a realize Davey, that ain't sayin' much."

"Come on, Jack. These boys worship you." He waved his arm, motioning towards the newsies gathered. "They'd do anything for you! Don't sell yourself short."

"I'm all they have, Davey. Don't mean I'm good at it, just means they haven't found someone better." He readjusted the strap on his bag before nodding, "Come on, we can't stand around here yappin' all day, we got papes to sell." Then he purposefully strode away.

David stood there for a moment, mouth slightly open. What was Jack saying? No one would argue the fact that he was the best leader Manhattan had ever had, in fact, he'd actually heard a few of the older boys say it! And every borough knew that Jack's boys were the happiest, knowing a freedom that few other leaders allowed their newsies to feel. Jack was one of the few people Davey ever knew to give up food, and even money, for someone else.

Of course, the boys loved Jack. Of course, he was the best thing to ever happen to them. Why didn't Jack believe it?

**~TH~**

**I only have one more chapter written, so if you have any ideas, please let me know! You can comment, DM me, or sent an Ask (on Tumblr) if you think of anything. Just tell me the insecurity, character, pre/post-strike, and let me know if you have a specific backstory idea or if you just want me to come up with something. **

**Next Chapter: Katherine tries to understand why Jack breaks up with her.**

**Love you guys! **

**Please please please comment!**

**God bless,  
Jamie**


	4. Katherine

**And here we have Katherine trying to figure out why Jack broke up with her.**

**WARNINGS: None that I can think of... Nothing worse than Pulitzer says to Jack in the Musical.**

**~TH~**

Jack hadn't moved. He hadn't held her hand or kissed her cheek or flirted once. He simply sat on the park bench, unmoving. Ever since they had left her house tonight, he had been off. Something wasn't right.

She reached for his hand, he didn't move away, but his hand twitched. She pulled her own back. "Jack, is everything okay?"

"I can't do this to you anymore."

_"Ah, Mr Kelly." Pulitzer looked up from his desk as Jack walked in._

_The boy gave a nervous smile. "You wanted to see me, Joe? I normally just drop my drawing off at the desk."_

_"Yes," The older man returned the smile with false sincerity. "I need to speak to you about my daughter."_

_"Ace?" Pultizer had his attention now._

_"Yes," he hissed, "Katherine. I know you have been... courting her the last several months,"_

_Jack nodded, "Yeah, so?"_

_"Really Mr Kelly? Are you really so naive to think you are good for her?"_

_The boy froze. He knew Pulitzer disapproved of him, but this was the first time he ever said something directly to him about it._

_"I've stood by, Mr Kelly. I've stood by and watched as you stole my daughter's heart. I assumed one of you would gain some common sense and back away, but now that it is clear that no such thing will be happening, I decided it was time to interfere. You will never be good enough for her."_

_Jack took a step back, "With all due respect Mr Pulitzer, I think Katherine is plenty capable of making her own decisions."_

_"I won't deny that Mr Kelly." The older man paused as if thinking. "Do you love her?"_

_"Ace?" Jack said in surprise, "'Course I do."_

_"Then how don't you see that she deserves so much better than you could ever offer her? You act as though you have everything planned, but I must ask, how do you plan on affording a place to stay? What about clothes? I assure you, woman are not content with one outfit, they need many. And food, Katherine has always been served the highest quality in every aspect. How do you plan to support her? She comes from an upper-class life and still doesn't realize that a life with you would bring her to the very bottom. It's easy to say you are in love and will care for her while she is still living under my roof, but how long will that last outside of it?"_

_Jack didn't move. He could feel his breathing becoming erratic. Joe was right. He couldn't do that to her._

_"I suggest you cut it off now before one of you gets hurt. You will never be good enough for my daughter, Mr Kelly, it's high time you realize that yourself."_

"Can't do what Jack? She asked, brushing a stray piece of hair behind her ear.

He stood up and began pacing. "I can't- I can't give you what you deserve. I can't even give you what you need! You deserve better than me, Ace. You deserve so much better!"

"No, Jack," She walked up, wrapping her arms around him. "You're plenty good enough for me."

He pulled away, "No! I-I'm not! One day, you're gonna wake up and realize that you could've had anyone, but you were stuck with me. You're gonna realize that I ain't good enough for ya, I never was, and you'd be right!" He sunk back down onto the bench, "You'd be right."

"Jack," Katherine sat beside him, latching onto his arm, "Don't say that. It's not true. I love you Jack Kelly and I'll never leave you."

"But you gotta Katherine!" She was surprised by the use of her real name. Jack was serious, "It can never work. I'm not good enough for you. How can you not see that? I'm a Newsie, Ace. I'm an orphan who's been in jail multiple times. You need someone who will be able to take care of ya. Who can give you everything you ever want. But you gotta go find him."

Katherine could feel the tears running down her cheeks. "I already found him. I don't want anyone else, I want you."

"No," Jack shook his head, untangling himself from her arms, "no, it will never work. I love you, Ace, more than I've ever loved anyone in my life, because of that I gotta let you go." He began to walk away. She could see him crying, she wanted to comfort him but she couldn't.

"Jack!" He didn't turn around, he just kept walking.

Had he just... broken up with her?

She sobbed angry tears. She was angry at Jack. She was so angry. Until she reached her home. She fell into her father's embrace as he offered her comfort. That's when she realized, he didn't seem the least bit surprised. She hadn't even told him what happened.

Katherine excused herself to her room. She started crying again, not angry this time, sad. Sad for herself, but even more for her Jack. What had her father said to make him do that? How could he honestly think he wasn't good enough for her? He was everything she had ever wanted in a man!

She would get him back. She had to.

**~TH~**

**This is the last one I have, so if you like this style, send prompts!**

**If you leave a comment you might be my new best friend 😁**

**Thanks for reading!**

**God bless,**  
**Jamie**


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